WO2014081134A1 - Nouveau composé et élément électroluminescent organique comprenant ledit composé - Google Patents

Nouveau composé et élément électroluminescent organique comprenant ledit composé Download PDF

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WO2014081134A1
WO2014081134A1 PCT/KR2013/009876 KR2013009876W WO2014081134A1 WO 2014081134 A1 WO2014081134 A1 WO 2014081134A1 KR 2013009876 W KR2013009876 W KR 2013009876W WO 2014081134 A1 WO2014081134 A1 WO 2014081134A1
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mol
aryl
synthesis
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김성무
배형찬
백영미
신진용
박호철
이창준
김영배
김태형
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주식회사 두산
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Definitions

  • the present invention relates to a novel organic compound that can be used as a material of the organic electroluminescent device and an organic electroluminescent device comprising the same.
  • the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine.
  • the material included in the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to its function.
  • the light emitting material may be classified into blue, green, and red light emitting materials according to the light emitting color, and yellow and orange light emitting materials required to realize a better natural color.
  • a host / dopant system may be used as a light emitting material to increase luminous efficiency through an increase in color purity and energy transfer.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer.
  • a phosphorescent dopant material used in the light emitting layer metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 are known, and as a phosphorescent host material, 4,4-dicarbazolybiphenyl (CBP) is known.
  • the existing materials have advantages in terms of light emission characteristics, but the thermal stability is low due to the low glass transition temperature, and thus the materials are not satisfactory in terms of lifespan of the organic EL device.
  • an object of the present invention is to provide an organic electroluminescent device having improved driving voltage, luminous efficiency and the like by including the novel organic compound.
  • the present invention provides a compound represented by the following formula (1).
  • R 4 and R 5, R 5 and R 6 , or one of R 6 and R 7 may be combined with Formula 2 to form a condensed ring,
  • the dotted line represents a site where condensation occurs with the compound of Formula 1.
  • R 1 to R 11 and Ra are each independently hydrogen, deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 1 -C 40 alkylsilyl group, C 1 -C 40 alkylboron group, C 6 -C 40 aryl boron group, C 6- C 40 aryl phosphine group, is selected from the group consisting of C 6 ⁇ C 40 aryl phosphine oxide group, and a C 6 ⁇ C 40 aryl group in the silyl, by combining groups of neighboring may
  • n is an integer from 0 to 4,
  • Ar 1 is C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 40 Aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 40 aryl amine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 hetero cycloalkyl group, C 1 ⁇ C 40 alkyl silyl group, a alkyl boronic of C 1 ⁇ C 40, C 6 ⁇ C 40 aryl boron group, C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ aryl phosphine oxide of the C 40 group And it is selected from the group consisting of C 6 ⁇ C 40 arylsilyl group,
  • Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 C 40 alkynyl group, C 6 ⁇ C 40 aryl group, heteroaryl group of 5 to 40 nuclear atoms, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 -arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3
  • the present invention is an organic electroluminescent device comprising an anode, a cathode and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer comprises the compound An electroluminescent device is provided.
  • alkyl is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, Hexyl etc. are mentioned.
  • alkenyl is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon double bonds. Examples thereof include vinyl and allyl. (allyl), isopropenyl, 2-butenyl, and the like.
  • Alkynyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having one or more carbon-carbon triple bonds, and examples thereof include ethynyl, 2-propynyl etc. are mentioned.
  • aryl refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings.
  • a form in which two or more rings are attached to each other (pendant) or condensed may also be included. Examples of such aryls include phenyl, naphthyl, phenanthryl, anthryl and the like.
  • Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are simply attached or condensed with each other may be included, and is also construed to include a form condensed with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, 2-furany
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl and has a linear, branched or cyclic structure.
  • R'O- monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl and has a linear, branched or cyclic structure.
  • alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • Cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • Examples of such cycloalkyl include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.
  • Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se.
  • heterocycloalkyl include morpholine, piperazine and the like.
  • alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 5 to 40 carbon atoms
  • Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the novel compound according to the present invention is a structure in which an indole moiety is fused to an end of an indoloindole moiety to form a basic skeleton, and various substituents are bonded to the basic skeleton. It is characterized by being displayed as 1.
  • the compound of Formula 1 has a wide bandgap due to the indole moiety bound to the end of the indoloindole moiety, as well as the bipolar characteristics of the entire molecule due to various aromatic ring substituents.
  • the binding force between the holes and the electrons can be increased, the phosphorescence property of the organic EL device can be improved, and the luminous efficiency as well as the hole injection ability and the transport ability can be improved.
  • the molecular weight of the compound is significantly increased due to the various aromatic ring substituents introduced into the indole moiety, thereby improving the glass transition temperature, which is why the conventional CBP (4,4-dicarbazolybiphenyl) It can have high thermal stability.
  • the thermal stability of the compound is improved by the indole moiety fused to the end of the indoloindole moiety, and is effective in suppressing crystallization of the organic material layer. Therefore, the organic electroluminescent device including the compound of Formula 1 according to the present invention may greatly improve durability and lifespan characteristics.
  • the compound represented by Chemical Formula 1 of the present invention when used as a material for the hole injection / transport layer of an organic EL device, and is used as a phosphorescent host material of blue, green, and / or red, it has excellent efficiency and lifespan in comparison with conventional CBP. It can be effective. Therefore, the compound represented by Formula 1 of the present invention can greatly contribute to the performance improvement and lifespan improvement of the organic electroluminescent device, and the improvement of the life of the organic electroluminescent device can lead to the maximization of the performance in the full color organic light emitting panel.
  • the compound represented by Chemical Formula 1 of the present invention is preferably selected from the group consisting of compounds represented by the following Chemical Formulas 3 to 8 when considering the characteristics of the organic electroluminescent device.
  • R 1 to R 11 , Ra, Ar 1 and n are the same as defined above.
  • Ar 1 of the compound represented by the formula (1) of the present invention is C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 40 Aryl group, nucleus Heteroaryl group of 5 to 40 atoms, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, C 3 ⁇ C 40 cycloalkyl group, nucleus A heterocycloalkyl group having 3 to 40 atoms, a C 1 to C 40 alkylsilyl group, a C 1 to C 40 alkyl boron group, a C 6 to C 40 aryl boron group, a C 6 to C 40 arylphosphine group, C 6 ⁇ C 40 aryl phosphine oxide of the group and a C 6 ⁇ C 40 aryl group are selected from the silyl group consisting of, when
  • R 1 to R 11 and Ra of the compound of formula 1 according to the present invention are each independently selected from the group consisting of hydrogen or a structure represented by the following S1 to S206.
  • Ar 1 of the compound of Formula 1 according to the present invention is preferably selected from the group consisting of the structures represented by S1 to S206, S1, S6, S14, S19, S23, S71, S72, S78, S79, S80, S81, S84, S90, S91, S92, S95, S102, S103, S104, S105, S106, S107, S110, S112, S119, S122, S126, S127, S130, S139, S145, S146, S147, S148, S149, S150, S166, S167, S168, S169, S170, S175, S176, S177, S178, S179, S180, S181, S188, S197, S198, S199, S200, S201, S202, S203, S204, S205 and S206 More
  • the compound of formula 1 of the present invention can be synthesized in various ways with reference to the following synthesis examples. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
  • the present invention provides an organic electroluminescent device comprising a compound represented by Formula 1, preferably a compound represented by Formula 3 to Formula 8.
  • the present invention is an organic electroluminescent device comprising an anode (anode), a cathode (cathode) and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic material layer is It includes a compound represented by the formula (1), preferably a compound represented by the formula (3) to (8).
  • the compound of Formula 1 may be used alone or in combination of two or more.
  • the at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer may include a compound represented by the formula (1).
  • the organic material layer containing the compound of Formula 1 is preferably a light emitting layer.
  • the light emitting layer of the organic electroluminescent device of the present invention may include a host material, and may include the compound of Formula 1 as the host material.
  • the compound of Chemical Formula 1 when included as a light emitting layer material of the organic EL device, preferably a blue, green, or red phosphorescent host material, the binding force between the holes and the electrons in the light emitting layer is increased, thereby increasing the efficiency of the organic EL device. Luminous efficiency and power efficiency), lifetime, brightness and driving voltage can be improved.
  • the structure of the organic EL device according to the present invention is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
  • at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer comprises a compound represented by the formula (1) Can be.
  • the compound represented by Formula 1 of the present invention may be used as a phosphorescent host material of the light emitting layer.
  • the electron injection layer may be further stacked on the electron transport layer.
  • the structure of the organic electroluminescent device according to the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device according to the present invention may be formed using other materials and methods known in the art, except that one or more layers (eg, a light emitting layer) of the organic material layer are formed to include the compound represented by Chemical Formula 1. It can be prepared by forming an organic layer and an electrode.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
  • examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
  • metals such as vanadium, chromium, copper, zinc and gold or alloys thereof.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • IC-3 (3.0 g, 9.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.99 g, 11.16 mmol), and NaH (0.27), which were the compounds prepared in Preparation Example 2, under a nitrogen stream. g, 11.16 mmol) and DMF (80 ml) were mixed and stirred at room temperature for 3 hours. After the reaction was completed, water was added, the solid compound was filtered, and the residue was purified by column chromatography to obtain Com-1 (3.2 g, yield 62%) as a target compound.
  • a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • Example 2 The same procedure as in Example 1 was repeated except that the compounds Com-2 to Com-65 synthesized in Synthesis Examples 2 to 65 were used instead of the compound Com-1 used as a host material in forming the emission layer in Example 1. The device was manufactured.
  • a device was manufactured in the same manner as in Example 1, except that the following CBP was used instead of the compound Com-1 used as a host material in forming the emission layer in Example 1.
  • the green organic electroluminescent device (Examples 1 to 65) using the compound represented by Formula 1 of the present invention as a host material of the light emitting layer is a green organic electroluminescent device using a conventional CBP as a host material (Comparative Example It was confirmed that the better performance in terms of current efficiency and driving voltage than).
  • the compound represented by Chemical Formula 1 of the present invention may be used as a material of the organic material layer of the organic EL device because of its excellent thermal stability and phosphorescence properties.
  • the compound represented by Chemical Formula 1 of the present invention when used as a phosphorescent host material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency and long life compared to a conventional host material can be manufactured, and further, performance And a full color display panel with greatly improved lifespan.

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  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention concerne un nouveau composé organique et un élément électroluminescent organique comprenant ledit composé, et peut fournir un élément électroluminescent organique ayant des caractéristiques améliorées telles qu'une efficacité lumineuse, une tension de commande et une durée de vie par introduction, dans l'élément électroluminescent organique, d'une couche électroluminescente dans laquelle un composé à base d'indole est utilisé comme substance hôte.
PCT/KR2013/009876 2012-11-21 2013-11-04 Nouveau composé et élément électroluminescent organique comprenant ledit composé WO2014081134A1 (fr)

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KR1020120132282A KR101577100B1 (ko) 2012-11-21 2012-11-21 신규 화합물 및 이를 포함하는 유기 전계 발광 소자
KR10-2012-0132282 2012-11-21

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CN105061436A (zh) * 2015-09-10 2015-11-18 清华大学 一种多取代稠合吲哚并吲哚类化合物的制备方法
WO2016036171A1 (fr) * 2014-09-04 2016-03-10 Rohm And Haas Electronic Materials Korea Ltd. Pluralité de matériaux hôtes et dispositifs électroluminescents organiques les comprenant
KR20160028979A (ko) * 2014-09-04 2016-03-14 롬엔드하스전자재료코리아유한회사 복수종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자

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WO2017142308A1 (fr) * 2016-02-15 2017-08-24 주식회사 엘지화학 Composé hétérocyclique et dispositif électroluminescent organique le comprenant
KR102559638B1 (ko) * 2016-05-24 2023-07-26 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
CN113015733B (zh) * 2019-01-25 2023-11-14 株式会社Lg化学 化合物和包含其的有机发光器件

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016036171A1 (fr) * 2014-09-04 2016-03-10 Rohm And Haas Electronic Materials Korea Ltd. Pluralité de matériaux hôtes et dispositifs électroluminescents organiques les comprenant
KR20160028979A (ko) * 2014-09-04 2016-03-14 롬엔드하스전자재료코리아유한회사 복수종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자
KR102409002B1 (ko) 2014-09-04 2022-06-16 롬엔드하스전자재료코리아유한회사 복수종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자
CN105061436A (zh) * 2015-09-10 2015-11-18 清华大学 一种多取代稠合吲哚并吲哚类化合物的制备方法
CN105061436B (zh) * 2015-09-10 2017-08-11 清华大学 一种多取代稠合吲哚并吲哚类化合物的制备方法

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KR101577100B1 (ko) 2015-12-11

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